Reaktion #565180

ord-b9f2f5421b4d4569a6509ea5288ef395

Reaktionsgleichung

[N-]=[N+]=N
hydrazoic acid
O=C(O)c1ccc(C2CCCc3cncn32)cc1
5-(p-carboxyphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine
O=S(=O)(O)O
sulfuric acid
Nc1ccc(C2CCCc3cncn32)cc1
title compound
Nc1ccc(C2CCCc3cncn32)cc1
5-(p-Aminophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]-pyridine

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction mixture is heated to 40°
  2. 2
    Sonstigethe reaction mixture is evaporated
  3. 3
    workup.DISSOLUTIONThe residue is redissolved in water
  4. 4
    ExtraktionThe aqueous phase is extracted with methylene chloride (3×30 ml)
  5. 5
    TrocknenThe organic extracts are dried over potassium carbonate
  6. 6
    Sonstigeevaporated

Vorschrift

A solution of 2.42 g of 5-(p-carboxyphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 100 ml of ethylene dichloride is treated with 6 ml of concentrated sulfuric acid. The reaction mixture is heated to 40° and 6 ml of hydrazoic acid (2M in ethylene dichloride) is added dropwise. When gas evolution has ceased, the reaction mixture is evaporated. The residue is redissolved in water and adjusted to pH 10. The aqueous phase is extracted with methylene chloride (3×30 ml). The organic extracts are dried over potassium carbonate and evaporated to yield the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04889861uspto-grants-1989_12